Isosorbide 5-mononitrate Chemical Properties

Melting point:

88-93 °C

alpha 

170 º (c=1, EtOH)

Boiling point:

326.86°C (rough estimate)

Density 

1.5784 (rough estimate)

refractive index 

145 ° (C=5, H2O)

storage temp. 

-20°C Freezer

solubility 

Undiluted isosorbide mononitrate is freely soluble in water, in acetone, in ethanol (96 per cent) and in methylene chloride. The solubility of the diluted product depends on the diluent and its concentration.

pka

13.09±0.40(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

soluble

Merck 

5225

InChIKey

YWXYYJSYQOXTPL-SLPGGIOYSA-N

CAS DataBase Reference

16051-77-7(CAS DataBase Reference)

EPA Substance Registry System

D-Glucitol, 1,4:3,6-dianhydro-, 5-nitrate (16051-77-7)

Safety Information

Hazard Codes 

Xi-F,Xi,F

Risk Statements 

36/37/38-11

Safety Statements 

37/39-16-15

RIDADR 

3251

RTECS 

LZ4386500

HazardClass 

4.1

HS Code 

2932999000

Toxicity

LD50 oral in rat: 2010mg/kg

MSDS

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Isosorbide 5-mononitrate Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

antidepressant, 5HT reuptake inhibitor

Uses

Isosorbide 5-Mononitrate is a metabolite of Isosorbide Dinitrate; used as an antianginal.

Uses

A metabolite of Isosorbide Dinitrate. Used as an antianginal

Definition

ChEBI: Isosorbide mononitrate is a nitrate ester and a glucitol derivative. It has a role as a nitric oxide donor and a vasodilator agent.

brand name

Imdur (Schering-Plough); Ismo (Dr. Reddy’s); Monoket (Schwarz Pharma) .

General Description

Isosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion.

Air & Water Reactions

Highly flammable.

Reactivity Profile

The dinitrate, a heart drug, can detonate when dry, but is non explosive with 30% of water [J. Haz.. Mater., 1992, 32(1), 87]. The mononitrate would be expected to be less reactive.

Health Hazard

Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.

Clinical Use

Vasodilator:
Treatment and prophylaxis of angina
Adjunct in congestive heart failure

Synthesis

The general procedure for the synthesis of isosorbide 2-nitrate from isosorbide (stored below +4°C) is as follows: 146 g of dehydrated sorbitol was dissolved in 880 mL of anhydrous ethyl acetate, stirred well, and then cooled to -5 to 0°C. Subsequently, 170 g of silver nitrate solids were added, stirring was continued, and 120 g of thionyl chloride was added dropwise at a slow rate. After the dropwise addition was completed, the reaction mixture was stirred at the same temperature for 10 hours. Upon completion of the reaction, the reaction process was monitored by high performance liquid chromatography (HPLC). The reaction solution was filtered by suction filtration. The filtrate was washed to neutrality with 500 mL of water to purify the product. The organic phase was dried with 20 g of anhydrous magnesium sulfate for 4 hours. After drying, the magnesium sulfate was removed by filtration and the filtrate was decolorized by adding 17.6 g of activated carbon and heated to reflux for 30 minutes. After the decolorization was completed, the activated carbon was removed by filtration and the filtrate was concentrated to dryness by decompression to give 170 g of isosorbide 2-nitrate solid. The purity of the product was 99.85% and the yield was 89.0% by HPLC analysis.

References

[1] Patent: CN107011354, 2017, A. Location in patent: Paragraph 0042-0057
[2] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 12, p. 1809 - 1810
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 9, p. 793 - 795
[4] ChemMedChem, 2015, vol. 10, # 10, p. 1724 - 1732

Isosorbide 5-mononitrate(16051-77-7)Related Product Information

• Isosorbide
• Isosorbide dinitrate
• ISOSORBIDE 2-MONONITRATE,ISOSORBIDE 2-MONONITRATE 99-101.0%
• Sodium hydride
• Sorbitol
• NIVITIN DEHYDROGENASE
• Prenyl acetate
• isosorbide-5-mononitrate-2-glucuronide
• ISOSORBIDE-13C6 DINITRATE
• Isosorbide 5-mononitrate